4-Methoxy-2-nitrophenyl isothiocyanate → (1,1-dimethyl ethyl) N-[[(2-amino-4-methoxyphenyl)amino]thioxomethyl]-O-(4-ethoxy-4-oxobutyl)-L-tyrosinate

HRID 1759696노트

반응식

HRID 1759696 반응식
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:24]=[CH:23][C:12]([CH2:13][C@@H:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[NH2:15])=[CH:11][CH:10]=1)[CH3:2].[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[S:36])=[C:30]([N+:37]([O-])=O)[CH:29]=1>C1COCC1>[NH2:37][C:30]1[CH:29]=[C:28]([O:27][CH3:26])[CH:33]=[CH:32][C:31]=1[NH:34][C:35](=[S:36])[NH:15][C@H:14]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:13][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:25])=[CH:24][CH:23]=1

참가 물질

4

반응물 2

HCID 1410064-Methoxy-2-nitrophenyl isothiocyanateHCID 15512208tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate

생성물 1

HCID 86594971(1,1-dimethyl ethyl) N-[[(2-amino-4-methoxyphenyl)amino]thioxomethyl]-O-(4-ethoxy-4-oxobutyl)-L-tyrosinate수율 99.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The aminoester 4-2 (350 mg, 1 mmole) in 20 ml of THF is mixed with 4-methoxy-2-nitrophenyl isothiocyanate (210 mg, 1 mmole), followed by agitating for 1 hour at ambient temperature, evaporating under reduced pressure, then adding SnCl2 (380 mg then 190 mg, 3 mmoles) in 10 ml of DMF and agitating for 4 hours at ambient temperature. After evaporating under reduced pressure and taking up in a water/NaHCO3/AcOEt mixture, decanting, drying the organic phase and evaporating under reduced pressure, 530 mg of crude product is obtained.

후처리

  1. customevaporating under reduced pressure
  2. stirringadding SnCl2 (380 mg then 190 mg, 3 mmoles) in 10 ml of DMF and agitating for 4 hours at ambient temperature
  3. customAfter evaporating under reduced pressure
  4. customdecanting
  5. customdrying the organic phase
  6. customevaporating under reduced pressure

출처 및 근거

ORD 기록
ord-0d91d8e15271485787418d66c687e1f3
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06838453B2

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